Nice guys finish first

“When you work in show business, you get paid stupid money for silly things,” Jay Leno says in a recent Hollywood Reporter podcast interview.

Of course, entertainment success involves being in the right place at the right time, and Leno views the current late-night landscape with its heavy emphasis on Trump-bashing as not being the place where he would feel comfortable.

Jay Leno with President Barack Obama in April 2009. Photograph by Pete Souza.

“I was lucky,” he continues in his podcast chat. “I did it at a time when Bush was dumb and Clinton was horny … I don’t like Trump, I can’t stand the guy, I don’t like him personally. But the constant negative Trump stuff on a nightly basis? I think it has a debilitating effect on people. People are just, ‘Oh, gosh, I don’t wanna watch TV anymore. This is just the same thing every night.’”

In early November, the former host of “The Tonight Show” was certainly in the right place at the right time, headlining “The Really Big Show” at Purchase College’s Performing Arts Center, which raised funds for the Big Brothers Big Sisters of Family Services of Westchester. For Leno, the event was a homecoming of sorts: He was born and spent his first nine years in New Rochelle, and the gala returned him to the stand-up format where he has reigned for four decades and continues to appear in an average of 210 engagements annually.

“There’s not a lot of money for kinds of things like this, so it’s up to private people to help out when they can,” Leno told reporters in a press event ahead of the Purchase event. “It’s a terrific organization and you don’t really see the fruits of it until 20 or 30 years later when someone says, ‘I got to go to this college because of something you did or program you set up,’ so that’s what makes you feel good.”

And perhaps that’s also the secret to Leno’s longevity — making people feel good. Unlike the present crop of late-night hosts who seem fixated on telling people how to vote, Leno would offer his “Tonight Show” viewers the opportunity to end their days with a laugh instead of a lecture. For more than two decades, there were few complaints from viewers — his ratings were nearly always ahead of rival David Letterman, whom he beat out as Johnny Carson’s “Tonight Show” successor. And if Leno had a negative comment about a politician or celebrity who was behaving badly, it would be the subject of a quick one-liner before zooming to another topic, not the focus of an entire monologue. Even today, Leno carefully balances political wisecracks on both sides of the aisle.

Indeed, Leno’s nice-guy attitude can play to his advantage when he occasionally sneaks in a very un-Leno remark. He drew both gasps and laughs at a recent show in Worcester, Massachusetts, when he dared to take on the region’s sports icons: “A liar, a cheater and a murderer walk into a bar. The bartender says, ‘Hey, the Patriots are in town.’”

More remarkable were Leno’s recent comments in another Hollywood Reporter piece published ahead of Letterman’s receiving the Mark Twain Prize. “The best days of my career were doing ‘Late Night With David Letterman,’” he recalls warmly, adding praise for his perceived foe in a self-deprecating manner. “I’m thrilled that Dave is getting the Mark Twain award. It’s a great award. It’s Mark Twain. And it gives my Mark Twain Prize credence.”

Jay Leno. Photograph by Chris Yarzab / Creative Commons.

But whereas Letterman has returned from his late-night retirement in occasional (and, seemingly, cranky) appearances — he offered no tribute when Leno won his Mark Twain Prize in 2015 — Leno moved into a charming next chapter with “Jay Leno’s Garage,” a leisurely program on CNBC and YouTube that mixes his love for classic cars and invigorating conversation. And if that audience is smaller than his “Tonight” following, Leno is not going to retreat into anxiety worrying about his legacy.

“Luckily, you as a performer don’t live on,” he told The New York Times earlier this year. “You die, eventually. If you’re worried about your legacy? Oh, shut up. Nobody cares. I was in Vegas and they were taking down an Elvis Presley exhibit at one of the hotels. I said, ‘What’s going on?’ They said, ‘We’re taking this down, the kids don’t really know who this is anymore.’ If you don’t know who Elvis is, I don’t think my legacy is something you have to worry about.”

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Phil Hall is the host of the SoundCloud podcast "The Online Movie Show," the author of seven books, including "The Greatest Bad Movies of All Time" and "In Search of Lost Films," a former United Nations radio correspondent for Fairchild Broadcast News, and a writer with credits in The New York Times, New York Daily News, Wired and The Hill's Congress Blog.